N-{2-[(2,4-Dibromo-6-nitrophenyl)diazenyl]-5-(diethylamino)phenyl}acetamide → Disperse Red 82

HRID 1701275Notes

Reaction equation

HRID 1701275 reaction equation
[C:1]([NH:4]C1C=C(C=CC=1N=NC1C([N+]([O-])=O)=CC(Br)=CC=1Br)N(CC)CC)(=O)C.Br[C:30]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[CH:32][C:31]=1[N:39]=[N:40][C:41]1[CH:59]=[CH:58][C:44]([N:45]([CH2:52][CH2:53][O:54][C:55](=[O:57])[CH3:56])[CH2:46][CH2:47][O:48][C:49](=[O:51])[CH3:50])=[CH:43][CH:42]=1>>[C:1]([C:30]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[CH:32][C:31]=1[N:39]=[N:40][C:41]1[CH:59]=[CH:58][C:44]([N:45]([CH2:52][CH2:53][O:54][C:55](=[O:57])[CH3:56])[CH2:46][CH2:47][O:48][C:49](=[O:51])[CH3:50])=[CH:43][CH:42]=1)#[N:4]

Participants

3

Reactant 2

HCID 12525524N-{2-[(2,4-Dibromo-6-nitrophenyl)diazenyl]-5-(diethylamino)phenyl}acetamideHCID 20347453HCID 20347453, compound

Product 1

HCID 121639Disperse Red 82Yield 15.95%

Procedure

When the 3-acetylamino-4-(2',4'-di-bromo-6'-nitrophenylazo)-N,N-diethylaniline employed in Example 9 was replaced by 4-(2'-bromo-4'-nitrophenylazo)-N,N-di(β-acetoxyethyl)aniline (4.8 parts) reaction was effectively complete in 7 hours at 90° C. Isolation of the product by the method of Example 9 gave 4-(2'-cyano-4'-nitrophenylazo)-N,N-di(β-acetoxyethyl)aniline (Found: C, 57.4; H, 5.1; N, 16.1. C21H21N5O6 requires C, 57.4; H, 4.8; N, 15.95%).

Sources & evidence

ORD record
ord-62b0e25abd9b4846989fae8968ff11ae
Source dataset
uspto-grants-1980_03
Patent number
US04192800

Reaction notes

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